Methanol → HCID 15337848, compound

Participants

Reaction Conditions

Reaction Steps

To a flask was charged with phosphonic acid 1 (67 mg, 0.1 mmol), methanol (0.1 mL, 2.5 mmol) and 1,3-dicyclohexylcarbodiimide (83 mg, 0.4 mmol), then pyridine (1 mL) was added under N2. The resulted mixture was stirred at 60-70° C. for 2 h, then cooled to room temperature and diluted with ethyl acetate. The mixture was filtered and the filtrate was evaporated. The residue was diluted with ethyl acetate and the combined organic phase was washed with NH4Cl, brine and water, dried over Na2SO4, filtered and concentrated. The residue was purified by chromatography on silica gel (isopropanol/CH2Cl2, 1% to 7%) to give 2 (39 mg, 56%) as a white solid. 1H NMR (CDCl3) δ 7.71 (d, J=8.7 Hz, 2H), 7.15 (d, J=8.7 Hz, 2H), 7.00 (d, J=8.7 Hz, 2H), 6.87 (d, J=8.7 Hz, 2H), 5.65 (d, J=5.1 Hz, 1H), 5.10-4.92 (m, 4H), 4.26 (d, J=9.9 Hz, 2H), 3.96-3.65 (m overlapping s, 15H), 3.14-2.76 (r, 7H), 1.81-1.55 (m, 3H), 0.91 (d, J=6.6 Hz, 3H), 0.88 (d, J=6.6 Hz, 3H); 31P NMR (CDCl3) δ 21.7; MS (ESI) 723 (M+Na).

Provenance & Evidence